Montgomery Hotel Guide - Hotels with Pool in Montgomery, New York

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Check availability on Montgomery Hotels with Pool

Tonight
26 Dec - 27 Dec
Tomorrow
27 Dec - 28 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Montgomery hotels with a pool

Exterior
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Montgomery
10.0 out of 10, Exceptional, (2)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is €249
includes taxes & fees
8 Jan - 9 Jan 2026
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
BBQ/picnic Area
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1004)
"Room was clean and staff was great!"
United States
Annemarie
The price is €80
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn by Hilton Middletown
Indoor pool, pool loungers
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.4 out of 10, Very good, (1001)
"The breakfast was a hit, the place is clean and I would stay here again."
United States
elizabeth
The price is €84
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Sports facility
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1003)
"It was a great place to stay "
United States
Amanda
The price is €88
includes taxes & fees
12 Jan - 13 Jan 2026
Hilton Garden Inn Fishkill
Indoor pool
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1002)
"Yes stay was pleasant "
United States
henry
The price is €90
includes taxes & fees
1 Jan - 2 Jan 2026
Comfort Suites Fishkill near Interstate 84
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1003)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is €114
includes taxes & fees
1 Jan - 2 Jan 2026
Overlook Lodge at Bear Mountain
Seasonal outdoor pool, pool umbrellas, pool loungers
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is €294
includes taxes & fees
2 Jan - 3 Jan 2026
LEGOLAND Hotel NEW York
Indoor pool
Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie
3.0 star property
Poughkeepsie
9.4 out of 10, Exceptional, (395)
"Beautiful room and great staff! Would stay here again. "
United States
Christina
The price is €112
includes taxes & fees
2 Jan - 3 Jan 2026
Home2 Suites By Hilton Poughkeepsie
Indoor pool
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1000)
"The hotel was very clean, enjoyed my stay would recommend "
United States
Jessica
The price is €97
includes taxes & fees
11 Jan - 12 Jan 2026
Courtyard by Marriott Middletown Goshen
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very good, (1002)
"Love it, everytime we come this is the place to stay"
United States
William
The price is €97
includes taxes & fees
1 Jan - 2 Jan 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Montgomery Hotel Reviews

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

10/10 Excellent
"A nice, clean hotel perfect for a quick business/recreational trip"
Sharonda 1-night trip
Posted 5 days ago
Courtyard by Marriott Poughkeepsie

Frequently asked questions

What are some accommodation options with pools in Montgomery?
Holiday Inn Express & Suites Montgomery by IHG: Hotel, 7-minute walk from Resorts World Catskills. Features a children's pool, an indoor pool and a water park. Super 8 by Wyndham Montgomery Maybrook: Offers a full-service spa, a seasonal outdoor pool and a snack bar/deli. Borland House Inn: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool and complimentary high-speed (wired) Internet access. The Kartrite Resort & Indoor Waterpark: Hotel, 4-minute walk from Resorts World Catskills. Offers 6 restaurants, a pool and a full-service spa. Overlook Lodge at Bear Mountain: Provides a snack bar/deli, an indoor pool and buffet.
What is there to see and do in Montgomery?
Surround yourself with nature at Thomas Bull Memorial Park and Orange County Arboretum. During your stay, visit sights such as City Winery Hudson Valley, Highland Lakes State Park and Orange County Tennis Center. You'll also discover lots of options for restaurants in Montgomery.
When is the best time to book a hotel with a pool in Montgomery?
Taking the local weather in Montgomery into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Montgomery are January, February, March and April, with each month seeing an average of 16 cm of snowfall.